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Report | Regular issue | Vol 23, No. 6, 1985, pp.1451-1457
Published online, 1st January, 1970
DOI: 10.3987/R-1985-06-1451
Synthesis of the Alkaloids and Laurifonine Using a Chloroformate-madiated Ring Expansion

John B. Bremner* and Charles Dragar

*Department of Chemistry, University of Tasmania, GPO Box 252C Hobart, Tasmania, 7001, Australia


A convenient synthesis of the reduced dibenz[d,f]azonine ring system is described affording laurifonine in 29% overall yield from homoveratrylamine. The alkaloid laurifine is also accessible in 15% overall yield (as the oxalate salt) by the same route, which employs a methyl chloroformate-induced ring expansion of an erythrinan-3-one derivative.